Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 8.1, Problem 8.1E

(a)

Interpretation Introduction

Interpretation: Structure of 4-octanol should be drawn.

Concept introduction: In accordance with IUPAC systematic nomenclature of alcohols can be derived from the parent alkane with “e” dropped and replaced by “ol” suffix.

As per IUPAC recommendations, longest chain found in a continuous manner in a branched molecule is chosen as parent chain. The longest chain must contain the alcohol functional group.The chain carbons are numbered so as to provide least numeral position towards the end in vicinity to OH group.

In alkanes, the positions of side chains or alkyl substituents are indicated by lowest numeral places before prefix.

(b)

Interpretation Introduction

Interpretation: Structure of 2,2,2-trichloroethanol should be drawn.

Concept introduction:In accordance with IUPAC systematic nomenclature of alcohols can be derived from the parent alkane with “e” dropped and replaced by “ol” suffix.

As per IUPAC recommendations, longest chain found in a continuous manner in a branched molecule is chosen as parent chain. The longest chain must contain the alcohol functional group.The chain carbons are numbered so as to provide least numeral position towards the end in vicinity to OH group.

In alkanes, the positions of side chains or alkyl substituents are indicated by lowest numeral places before prefix.

(c)

Interpretation Introduction

Interpretation: Structure of (S)-3-methyl-3-hexanol should be drawn.

Concept introduction:In accordance with IUPAC systematic nomenclature of alcohols can be derived from the parent alkane with “e” dropped and replaced by “ol” suffix.

As per IUPAC recommendations, longest chain found in a continuous manner in a branched molecule is chosen as parent chain. The longest chain must contain the alcohol functional group.The chain carbons are numbered so as to provide least numeral position towards the end in vicinity to OH group.

In alkanes, the positions of side chains or alkyl substituents are indicated by lowest numeral places before prefix.

In order to assign absolute configuration of R and S, Cahn−Ingold−Prelog rules are used and the first step is to assign the priority order on the basis of atomic number. The one with highest atomic number gest highest priority and is designated as a and so on.

The Fischer projection is written along with the priorities assigned and groups are interchangedbetween adjacent places so as to obtain lowest priority group at the bottom or lowest priority.

If the groups now are arranged are read from highest towards least in clockwise fashion the R is assigned to the stereocenter, if the rotation is anticlockwise the S is assigned at the configuration.

(d)

Interpretation Introduction

Interpretation: Structure of trans-2-bromocyclopentanol should be drawn.

Concept introduction:In accordance with IUPAC systematic nomenclature of alcohols can be derived from the parent alkane with “e” dropped and replaced by “ol” suffix.

As per IUPAC recommendations, longest chain found in a continuous manner in a branched molecule is chosen as parent chain. The longest chain must contain the alcohol functional group.The chain carbons are numbered so as to provide least numeral position towards the end in vicinity to OH group.

In alkanes, the positions of side chains or alkyl substituents are indicated by lowest numeral places before prefix.

(e)

Interpretation Introduction

Interpretation: Structure of 2,2-dimethyl-1-propanol should be drawn.

Concept introduction:In accordance with IUPAC systematic nomenclature of alcohols can be derived from the parent alkane with “e” dropped and replaced by “ol” suffix.

As per IUPAC recommendations, longest chain found in a continuous manner in a branched molecule is chosen as parent chain. The longest chain must contain the alcohol functional group.The chain carbons are numbered so as to provide least numeral position towards the end in vicinity to OH group.

In alkanes, the positions of side chains or alkyl substituents are indicated by lowest numeral places before prefix.

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